10 Colorful Outfits For Cold and Grey Days
Jenna front-loads the cool weather outfits, this time in color!
The HAF-wit most likely to drop off in the winter has returned! I’m here, feeling the need to front-load some cool weather outfits.
As I have complained before, it’s a challenge to stay colorful in climates that require multiple layers for fear of the ensemble veering garish. I’ve been hard at work on this particular quandary, so much so that I’ve already spent a 62° day this season sweating out my overcorrection! That experience truly pained me, but the silver lining was the realization that I am slowly getting better at bundling up — without omitting too much of the rainbow.
Without further preamble, here are the outfits I’ve worn and plan to wear this fall:

Drab! the Musical, starring little pops of color. This isn’t the rainbow I promised you; most of this clothing belongs corralled on Auntie Em’s monochromatic farm. The overall ensembles have understated colorways, but each one’s dynamism depends on flourishes of red, yellow, and rich navy blue. This selection is from the beginning of fall, when I was still reacquainting myself with the sweaters in my closet and it will suffice against a backdrop of vibrant autumn leaves! Plus, I get a jolt whenever a new combination is unlocked, and these are four fresh fits from mostly tenured garments.
(1) was thrown together on the first cold, rainy day. Its assembly revealed a potential wardrobe hole, as I wasn’t totally satisfied with the compulsory rain boot in black: ISO charcoal grey, silver, or navy boots or sneakers for wearing with midnight blues.
(2) I threw on for the grocery store. One small detail of note: The v-neck on the sweater has ripped and I am repairing it (slowly) with red duplicate embroidery stitches. Maybe I will add rosettes to the yoke.
(3) features the hint of a red and green scheme that doesn’t read Christmas-y. Olive’s warm, grey tone complements the heat from the red. I draped my brown vintage leather bomber —seen below in Fit 5— over this look’s shoulders for additional warmth.
(4) served me well for errands run on a high 50s, low 60s day. I’m devastated to say that the black Armani trousers conceal HEATTECH worn too early, though they came in handy for later that mid-50° evening in (5) for Nas x Wu Tang at Barclays. I be tossin’ and flossin’, my style is awesome.1

As annoying as I find it to be on trend2, I can’t deny the punch that rude red is packing right now. Joining the red is stalwart oatmeal, off-white, and ruddy browns, while shades of purple like royal and lilac elevate it. I’m also partial to what I consider “true indigo,” as displayed in the Liz Claiborne cropped knit; The hue perfectly straddles blue and purple, so much so you can’t tell which it really is. Possibly it is a chromatic Room of Requirement, as in this assemblage it appears purple.
(1) came together in my need of a house party outfit that wouldn’t fall flat sans shoes. It’s also there for James-Lange purposes I’ve discussed before. Due to a background removal glitch, it looks like I’m wearing a black ribbon in my half done-up hair, which would be a nice addition.
(2) makes me feel like an urban cowboy, but in a Commission Fall 2022 way, not a John Travolta way. I button the Liz Claiborne cardigan creatively in order to produce a cropped silhouette to reveal the hem of the sleeveless button down just so.
(3) started with a purple ringer tee x slouchy cords x Mary Janes base that I call “late for soccer practice, late for ballet,” and is 100% early autobiographical. With relief, the red sweater worn as a scarf doesn’t add too much prep as long as it’s worn with a leather blazer.
(4) keeps it simple, depending on silver accessories and a peek-a-boo grey contrast tee for dimension and to prevent it from boring me.
(5) must be worn outside and pretty much in total, a Jenga fit. While I could do without the bowler bag (and utilize the jacket’s numerous pockets), removal of the leather bomber or scarf switches the vibe too drastically and flattens the color scheme. This fact could make it impractical, but I’ve worn this outfit three times already this season.
(6) sticks the landing on a proportions challenge: a hooded sweatshirt worn under a cardigan. I bought the vintage red hoodie in its children’s size for warmth in Tannersville, an impulsive and impractical choice if not for my penchant for oversized cardigans.
HEATTECH and a heavier, winter overcoat can supplement a good 8/10 outfits seen here for the fall-to-winter transition. See you on the other side!
Did you know the lyric is actually “I be tossin’, enforcin’, my style is awesome”? Frankly, STET. I like my version.
Welcome to “Tomato Girl Fall”?
This purple and red color palette is amazingly autumnal yet i never would’ve imagined it. You’re a walking embodiment of the best leaves of the season
Loving the purple, brown, and yellow palette-the color combination I didn't know I needed, but will be recreating post haste. I've also been pining for those yellow Onitsuka Tiger sneakers for months and after seeing your styling, I'm doubling down my search 🫡